Synthesis of Dibenzo[d,f][1,3]Diazepines via Elemental Sulfur-Mediated Cyclocondensation of 2,2′-Biphenyldiamines with 2‑Chloroacetic Acid Derivatives

The three-component reaction of 2,2′-biphenyldiamines with 2-chloroacetic acid derivatives and elemental sulfur was developed for the practical synthesis of unknown 2-carboxamide-substituted dibenzo­[d,f]­[1,3]­diazepines. This protocol is distinguished by efficiency in water and good tolerance to f...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-12, Vol.84 (24), p.15817-15826
Main Authors: Tikhonova, Tatyana A, Lyssenko, Konstantin A, Zavarzin, Igor V, Volkova, Yulia A
Format: Article
Language:English
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Summary:The three-component reaction of 2,2′-biphenyldiamines with 2-chloroacetic acid derivatives and elemental sulfur was developed for the practical synthesis of unknown 2-carboxamide-substituted dibenzo­[d,f]­[1,3]­diazepines. This protocol is distinguished by efficiency in water and good tolerance to functional groups and can be adapted to a large-scale synthesis. The chemoselective preparation of a variety of 2-S,N,O-substituted dibenzo­[d,f]­[1,3]­diazepines was accomplished using the developed method.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02002